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Some of the world's most famous golf architects, including Robert Trent Jones (both Jr. and Sr.), Pete Dye, and Gary Player, have designed challenging courses in the Caribbean.

  • Tierra del Sol Golf Course (Aruba; tel. 866/978-5158 in the U.S., or 297/586-0978; www.tierradelsol.com): Robert Trent Jones, Jr., has designed an 18-hole, par-71, 6,811-yard course that is one of the grandest in the southern Caribbean. On the northwest coast of this arid, cactus-studded island, the course takes in Aruba's indigenous flora, including the divi-divi tree.
  • Teeth of the Dog and the Links (Casa de Campo, Dominican Republic; tel. 809/523-3333; www.casadecampo.com.do): Teeth of the Dog is one of designer Pete Dye's masterpieces. Seven holes are set adjacent to the sea, whereas the other 11 are confoundedly labyrinthine. The resort also has a second golf course, the Links, which some claim is even more difficult.
  • Golf de St-François (Guadeloupe; tel. 590/88-41-87; www.lesilesdeguadeloupe.com): Six of its 18 holes are ringed with water traps, the winds are devilishly unpredictable, and the par is a sweat-inducing 71. This fearsome course displays the wit and skill of its designer, Robert Trent Jones, Sr. Most of the staff is multilingual, and because the course is owned by the local municipality, it's a lot less snobby than you might expect.
  • Tryall Club Jamaica (Montego Bay, Jamaica; tel. 876/956-5660; www.tryallclub.com): This is the finest golf course on an island known for its tricky breezes. The site occupied by the Tryall Club was once the home of one of Jamaica's best-known sugar plantations, the only remnant of which is a ruined waterwheel. The promoters of Johnnie Walker Scotch, who know a lot about golfing, use this place for their most prestigious competition. In winter the course is usually open only to guests of the Tryall Club.
  • Cinnamon Hill (Rose Hall, Jamaica; tel. 876/953-2984; http://cinnamonhilljamaica.com): This is one of the top five courses in the world, even though it faces tough competition in Montego Bay. The signature hole is no. 8, which doglegs onto a promontory and a green that thrusts about 180m (591 ft.) into the sea. The back 9, however, are the most scenic and most challenging, rising into steep slopes and deep ravines on Mount Zion.
  • Four Seasons Resort Nevis (Nevis; tel. 800/332-3442; www.fourseasons.com/nevis): We consider this our personal favorite in all of the Caribbean. It was carved out of a coconut plantation and tropical rainforest in the 1980s, and its undulating beauty is virtually unequaled. Designed by Robert Trent Jones, Jr., the course begins at sea level, rises to a point midway up the slopes of Mount Nevis, and then slants gracefully back down near the beachfront clubhouse. Electric carts carry golfers through a maze of well-groomed paths, some of which skirt steep ravines.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.